A calm lake with boats, a stone dock, and houses with a stone wall and trees in the background.

Holiday Homes in Chester

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Chester holiday homes

House | 3 bedrooms

Private Sea House Escape at Whynachts Cove

Private Sea House Escape at Whynachts Cove
2.0 star property
Tantallon
Private Sea House Escape at Whynachts Cove
House | 1 bedroom

Stunning Oceanfront Home With Private Water Access

Stunning Oceanfront Home With Private Water Access
2.0 star property
Head Of Saint Margarets Bay
Stunning Oceanfront Home With Private Water Access
House | 1 bedroom

Spyglass Seastead in Chester Basin

Spyglass Seastead in Chester Basin
2.0 star property
Western Shore
Spyglass Seastead in Chester Basin
House | 4 bedrooms

Wolfville Manor Acadia Downtown Theater Sauna

Wolfville Manor Acadia Downtown Theater Sauna
2.0 star property
Wolfville
Wolfville Manor Acadia Downtown Theater Sauna
House | 7 bedrooms

Historic Estate - Group Gatherings Retreats

Historic Estate - Group Gatherings Retreats
2.0 star property
Wolfville
Historic Estate - Group Gatherings Retreats
House | 4 bedrooms

Lakefront Luxury Retreat w Heated Pool Arcade

Lakefront Luxury Retreat w Heated Pool Arcade
2.0 star property
Hammonds Plains
Lakefront Luxury Retreat w Heated Pool Arcade
House | 7 bedrooms

Heritage Estate 1893 - Former Inn - Walk Downtown

Heritage Estate 1893 - Former Inn - Walk Downtown
2.0 star property
Wolfville
Heritage Estate 1893 - Former Inn - Walk Downtown
House | 7 bedrooms

Executive 7 Bedrooms 3 5 Bathrooms

Executive 7 Bedrooms 3 5 Bathrooms
2.0 star property
Bedford
Executive 7 Bedrooms 3 5 Bathrooms
House, Smoking | 3 bedrooms

Quiet and Convenient Retreat

Quiet and Convenient Retreat
2.0 star property
Bedford
Quiet and Convenient Retreat
House | 4 bedrooms

Lakefront Luxury Retreat w Heated Pool and Arcade

Lakefront Luxury Retreat w Heated Pool and Arcade
2.0 star property
Hammonds Plains
Lakefront Luxury Retreat w Heated Pool and Arcade
House | 4 bedrooms

Oceanfront Sanctuary Private Peaceful

Oceanfront Sanctuary Private Peaceful
2.0 star property
Northwest Cove
Oceanfront Sanctuary Private Peaceful
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Stardust Motel Bedford

Stardust Motel Bedford

10/10 Excellent
"Staff/Hosts were very helpful and available at all times. Room was immaculate! We will definitely return. Close to waterfront and shopping."
Colleen 2-night trip
Posted 8 hours ago
Stardust Motel Bedford

Find out more about Chester

Chester Holiday Homes information

Number of reviews
Accommodation
11 Holiday Homes
Lowest Price
Highest Price